Methyl 2-ethoxy-4,5-dinitrobenzoate → Methyl 4,5-diamino-2-ethoxybenzoate

HRID 1012126Notes

Reaction equation

HRID 1012126 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([N+:13]([O-])=O)=[CH:6][C:5]=1[O:16][CH2:17][CH3:18]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[CH:6][C:5]=1[O:16][CH2:17][CH3:18]

Participants

4

Reactant 1

HCID 71418202Methyl 2-ethoxy-4,5-dinitrobenzoate

Product 1

HCID 13913221Methyl 4,5-diamino-2-ethoxybenzoateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4,5-dinitro-2-ethoxy-benzoic acid methyl ester (320 mg) and 10% Pd/C (40 mg) in MeOH (8 mL) was stirred under an atmosphere of hydrogen gas for 4 h at r.t., filtered through a plug of Celite and reduced in vacuo to give the title compound (234 mg) as a black gum. 1H NMR (300 MHz, MeOD) δ 7.30 (s, 1H), 6.40 (s, 1H), 4.00 (q, 2H), 3.80 (s, 3H), 1.35 (t, 3H).

Workup

  1. filtrationfiltered through a plug of Celite

Sources & evidence

ORD record
ord-90af5fc7294e4ee69d3fbf4ace18a8ae
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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